JPH07304980A - Water-soluble azo compound, its production, and its use as dye - Google Patents

Abstract

PURPOSE: To obtain a water-soluble fiber-reactive azo dye for, especially, cellulosic fiber materials by using a specified azo compound.

CONSTITUTION: This azo dye is an azo compound represented by the formula (wherein M is H or a salt-forming metal; K is or a divalent residue derived by removing the group -N(R⁰) from a water-soluble coupling component (compound) H-K-N(R⁰)-H; R⁰ is H, a 1-4C alkyl or a sulfo-, carboxyl-, sulfato-, phosphato-, hydroxyl-, methoxyl-, ethoxyl-, phenyl-, monophosphophenyl-, or disulfophenyl-substituted 1-4C alkyl; G is a halogen; R¹ is H, a 1-4C alkyl, a sulfo-, carboxyl-, or like-substituted 1-4C alkyl, or the like; and R² is H, a 1-4C alkyl; or a sulfo-, carboxyl- or like-substituted 1-4C alkyl, or the like, or a phenyl substituted with 1-3 substituents (the substituents are two 1-4C alkyls, alkoxyls, or the like) or the like).

COPYRIGHT: (C)1995,JPO

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION This invention relates to fiber-reactive azo dyes.

[0002]

Fiber-reactive azo dyes having 2-aminonaphthalene disulfonic acid as a diazo component are disclosed, for example, in JP-A-59-133261 and JP-A-60-23.
453 and European Patent Application Publication No. 0128034.
Many are known from the specification, EP-A-0239847 and EP-A-0292955. Furthermore, European Patent Application Publication No. 05028
No. 93 and PCT-Patent application publication WO 91 /
No. 09913 (US Pat. No. 5,268,458) and PCT-Patent Application Publication No. WO 91/09914 (US Pat. No. 5,310,886) disclose 1-sulfo-6-carboxy-2-amino- as a diazo component. Fiber-reactive azo dyes with naphthalene are described.

[0003]

There is a constant expectation of improvements in the quality, economy and lightness of dyeings, and in this respect it is necessary to develop new azo dyes having improved properties and simple applicability. It was

[0004]

The present invention is based on the general formula (1)

[0005]

[Chemical 15]

Wherein M is hydrogen or a salt-forming metal, especially an alkali metal such as sodium, potassium or lithium, and K is a water-soluble coupling component (compound).
H-K-N (R ⁰ )-H is a divalent residue not containing a group of the formula -N (R ⁰ )-, wherein R ⁰ is hydrogen or alkyl having 1 to 4 carbon atoms, such as methyl. Or ethyl, or sulfo, carboxy, sulfato,
Alkyl having 1 to 4 carbon atoms substituted by phosphato, hydroxy, methoxy, ethoxy, phenyl, monosulfophenyl or disulfophenyl, eg ethyl, preferably hydrogen, G
Is halogen, such as fluorine or chlorine, preferably fluorine, R ¹ is hydrogen or alkyl having 1 to 4 carbon atoms, such as methyl or ethyl, or
Or alkyl having 1 to 4 carbon atoms substituted by sulfo, carboxy, phosphato, sulfato, hydroxy, cyano, phenyl or sulfophenyl, or phenyl, or sulfo, carboxy, 1 to 4 Alkyl having 1 carbon atom, alkoxy having 1 to 4 carbon atoms, phenyl substituted by chlorine and / or nitro, R ² is hydrogen or alkyl having 1 to 4 carbon atoms, for example Methyl or ethyl, or alkyl having 1 to 4 carbon atoms substituted by sulfo, carboxy, phosphato, sulfato, hydroxy, cyano, phenyl or sulfophenyl, or 1, 2 or 3 Substituent of Is 2 alkyl groups having 1 to 4 carbon atoms, such as ethyl, especially methyl, 2 alkoxy groups having 1 to 4 carbon atoms, such as ethoxy and methoxy, 1 bromine atom, 2 A chlorine atom, three sulfo groups, two carboxy groups, one nitro group, one alkylsulfonyl group having 1 to 4 carbon atoms, which is substituted or not with hydroxy ( For example β-hydroxyethylsulfonyl), one alkylamino group having 1 to 4 carbon atoms and hydroxy, sulfato, sulfo, phosphato in the alkyl residue, alkanoyloxy having 2 to 5 carbon atoms or alkylene Having 1 to 4 carbon atoms in the residue,
Carboxy-substituted alkanoyl amides, eg phenyl substituted by-, selected from the group consisting of 1 alkylamino group, having 1 to 4 carbon atoms, substituted or unsubstituted by succinamide Or R ² is monosulfonaphthyl, disulfonaphthyl or trisulfonaphthyl, or R ¹ and R ² together with the nitrogen atom are 3 to 8 carbon atoms, preferably 4 to 6 carbon atoms. Having an alkylene group or another hetero group, for example -N
Heterocyclic residues formed from H- or -O- groups and two alkylene groups having 1 to 4 carbon atoms, eg N-piperidino, N-piperazino or N-
Forming a morpholino) is provided.

Substituted alkylamino groups as substituents on the phenyl residue of R ² are, for example, β-sulfatoethylamino and β-succinamidoethylamino. Preferably -K-N (R ⁰ )-is represented by the general formula (2
a), (2b) or (2c)

[0008]

[Chemical 16]

(Wherein M and R ⁰ have the respective meanings given above, m is 1 or 2 and v is a direct covalent bond or the formula --NH--CO--phenylene, --NH--CO--).
NH- _{phenylene, - N (CH 3) -} CO- _{phenylene, - N (CH 3) -} CO- NH- phenylene or -
NH-phenylene), wherein in the general formula (2a), when m is 2, one of the sulfo groups is preferably bonded in the meta position to hydroxy, and The other is preferably linked in the para or meta position to the amino group and in the general formulas (2b) and (2c) the free bond leading to the azo group is preferably attached to the naphthalene nucleus in the ortho position to hydroxy. And the hydroxy group is
It is preferably bound to the naphthalene nucleus at the 8-position, while one sulfo group is preferably bound to the naphthalene nucleus at the 6-position and has the group -VNH- or -N (R
⁰ ) -is preferably attached to the naphthalene nucleus at the 2-position or the 3-position and when m is 2, the second sulfo group is attached to the naphthalene nucleus at the 3-position, particularly preferably at the 4-position. Are connected.

The groups "sulfo", "carboxy", "sulfato" and "phosphato" mentioned above and below include their acid form as well as their salt form. Thus, a sulfo group is a group corresponding to the general formula -SO ₃ M, a carboxy group is a group corresponding to the general formula -COOM, a phosphato group is a group corresponding to the general formula -OPO ₃ M ₂ , and a sulfato group. Is a group corresponding to the general formula —OSO ₃ M, in which case M has the abovementioned meaning.

In the general formulas (2b) and (2c),
The hydroxy group and the free bond are attached to each other in the same aromatic nucleus in the ortho position. Preferably the hydroxy group is attached to the naphthalene residue at the α-position.

Further preferred are azo compounds of general formula (1) in which -NR ¹ R ² is a heterocyclic residue as defined above, preferably N-morpholino. Further, -K-N (R ⁰ )-is represented by the general formula (3a) or (3b).

[0013]

[Chemical 17]

[Wherein M has the above-mentioned meaning and Z ⁰ represents the general formula (3A)

[0015]

[Chemical 18]

(Wherein G, R ¹ and R ² each have the above-mentioned meanings, particularly preferred meanings) and p is zero or 1 (when zero, this group is hydrogen). In the general formula (3a), one of the sulfo groups is bonded to the —NH—Z ⁰ group at the meta position or the para position, and the general formula (3b)
In the formula, -NH-Z ⁰ group is 2-position, 3-position or 4-position.
8-position in the 2-position or 3-position, preferably 2-position
Bound to a hydroxynaphthalene residue and p is 1
In the case of, the sulfo group is at the 3-position or the 4-position,
Preferably bonded to an 8-hydroxynaphthalene residue at the 4-position] is an azo compound which is a residue.

General formulas (1A), (1B), (1C) and (1D)

[0018]

[Chemical 19]

[Wherein M, G and p have the above-mentioned meanings, particularly preferred meanings, and a is 1, 2 or 3,
Preferably 2, b is 1, 2 or 3, preferably 2, X is oxygen or --NH--, R ³ is hydrogen, sulfo, carboxy, alkyl having 1 to 4 carbon atoms, For example ethyl, especially methyl, 1 to 4
Alkoxy having 1 carbon atom, eg ethoxy, especially methoxy or hydroxy and R ⁴ is hydrogen,
Sulfo, carboxy, alkyl having 1 to 4 carbon atoms, eg ethyl, especially methyl or 1 to 4
An alkoxy having 1 carbon atom, eg ethoxy, especially methoxy, wherein in the general formulas (1A) and (1B) the triazinylamino residue is attached to the 8-hydroxynaphthalene residue at the 2-position or the 3-position. And when p is 2, the sulfo group is attached to the 8-hydroxynaphthalene residue at the 3-position or the 4-position, preferably at the 4-position].

Further, the present invention provides a method for producing an azo compound represented by the general formula (1), wherein

[0021]

[Chemical 20]

A diazonium compound of an amine represented by the formula (wherein M has the above-mentioned meaning) is represented by the general formula (5):

[0023]

[Chemical 21]

## STR3 ## wherein K, R ⁰ , G, R ¹ and R ² each have the above-mentioned meaning, or the compound represented by the general formula (6)

[0025]

[Chemical formula 22]

A compound represented by the general formula (7) is prepared by formulating a compound represented by the formula (M, K and R ⁰ have the above-mentioned meanings).

[0027]

[Chemical formula 23]

Reacting with a compound represented by the formula (wherein G, R ¹ and R ² have the above-mentioned meanings),
Or general formula (8)

[0029]

[Chemical formula 24]

The compound represented by the formula (wherein M, K, R ⁰ and G have the above-mentioned meanings) is represented by the general formula HNR
^There is provided a method characterized by reacting with an amino compound represented by ¹ R ² (wherein R ¹ and R ² each have the above meaning).

The diazotization and coupling reactions of the process according to the invention are carried out in the customary manner, for example the diazotization is generally carried out at temperatures between -5 ° C. and + 15 ° C. and 2
The reaction is carried out at a lower pH and with sodium nitrite, preferably in an aqueous medium, and the coupling reaction is generally at a temperature of 0 to 30 ° C. and in the case of amino-containing coupling components 1 to 4.5. At a pH of 3 and, in the case of hydroxy-containing coupling components, at a pH of 3 to 7.5, preferably in an aqueous medium.

The condensation reaction of the amino starting compound of the general formula (6) with the compound of the general formula (7) can be carried out in a conventional manner by reacting the amino compound with a reactive halogen atom-containing triazine compound, for example organic or, preferably, Aqueous-organic media, particularly preferably aqueous media, with acid binders such as alkali metal or alkaline earth metal carbonates or alkali metal or alkaline earth metal bicarbonates or hydroxides or alkali metal acetates--alkali metal And the alkaline earth metal is preferably sodium, potassium or calcium-or is carried out in the presence of a tertiary amine such as pyridine, triethylamine or quinoline. If this condensation reaction is carried out in an organic or aqueous-organic medium, the organic solvent is acetone, dioxane or dimethylformamide. In particular, this condensation reaction is
10 ° C to + 60 ° C, preferably 30 ° C to 45 ° C
And a pH of 2 to 7, preferably 2 to 4.5. The reaction with the compound of the general formula (7), wherein G is fluorine, is particularly preferably carried out at a pH of 3 to 5 and a temperature of 0 ° C to 30 ° C.

The condensation reaction between the halotriazinylamino compound represented by the general formula (8) and the amino compound corresponding to the general formula HNR ¹ R ² is also known as a condensation reaction between a halotriazinylamino compound and an amine. It is carried out according to the method, for example with an acid binder in the reaction medium described above.
Generally this reaction is carried out at a temperature of 0 ° C. to 80 ° C. and a pH of 2 to 8, but in the case of starting compounds where Hal is a chlorine atom, the reaction is preferably 50
The reaction is preferably carried out at a temperature of 0 to 70 ° C and a pH of 2 to 4 and in the case of the starting compounds in which Hal is a fluorine atom, a temperature of 0 to 10 ° C and a pH of 6 to 8.

Starting compounds of the general formula HK-N (R ⁰ )-H are, for example, 1-amino-3,6- or -4,6-disulfo-8-naphthol, 7-amino-3- Sulfo-1
-Naphthol, 6-amino-3-sulfo--1-naphtho-
6-amino-3,5-disulfo-1-naphthol,
2-amino-4-acetylaminobenzene-1-sulfonic acid, 2-amino-8-naphthol-6-sulfonic acid,
6-methylamino-3-sulfo-1-naphthol, 6-
(4'aminophenyl) -amino-3-sulfo-1-naphthol and 1-amino-2,4-disulfo-8-naphthol.

Starting compounds corresponding to the general formula HNR ¹ R ² are, for example, 2-sulfoaniline, 3-sulfoaniline,
4-sulfoaniline, 2,4-disulfoaniline, 2,
5-disulfoaniline, 5-sulfo-2-methoxyaniline, 4-sulfo-2-methoxyaniline, 5-sulfo
-2-Methylaniline, 4-sulfo-2-methylaniline, 3-sulfo-4-methoxyaniline, 4-sulfo-
2-methoxy-5-methylaniline, 4-sulfo-2,
5-dimethoxyaniline, 5-sulfo-2,4-dimethoxyaniline, 4-sulfo-5-methoxy-2-methylaniline, 5-sulfo-2-chloroaniline, 3-sulfo-4-chloro-2-methylaniline 4-sulfo-5
-Chloro-2-methoxyaniline, 5- or 6-sulfo-2-aminonaphthalene, 6,8-disulfo-2-aminonaphthalene, 3,6,8-trisulfo-2-aminonaphthalene, 8-sulfo-2- Aminonaphthalene, 4,
6,8-Trisulfo-2-aminonaphthalene, 1,5-
Or 1,6-disulfo-2-aminonaphthalene, 4,
8-disulfo-2-aminonaphthalene, 6,7-disulfo-2-aminonaphthalene, 5,7-disulfo-2-aminonaphthalene, 5- or 6-sulfo-1-aminonaphthalene, 7-sulfo-1-amino Naphthalene, 1-sulfo-2-aminonaphthalene, 3,6- or 4,6-
Or 4,8-disulfo-1-aminonaphthalene, β-
Sulfoethylamine, β-hydroxyethylamine, N
-Methyl-N- (β-sulfatoethyl) -amine, N
-Methyl-N-ethylamine, dimethylamine, diethylamine, β-carboxyethylamine, 4-sulfobenzylamine, 4-sulfophenethylamine, benzylamine, 2-methylaniline, aniline, 4-chloroaniline, N-ethylaniline, N- Methylaniline, ammonia, morpholine, piperidine and piperazine.

Separation and isolation of the compound of the general formula (1) according to the present invention, hereinafter referred to as compound (1), from an aqueous synthesis solution is carried out by a method generally known for a water-soluble compound, for example, an electrolyte, It can be carried out, for example, by precipitation from the reaction medium with sodium chloride or potassium chloride or by evaporation of the reaction solution itself, for example spray drying.

When choosing the last-mentioned isolation method, it is often recommended to remove the sulfates present in the solution before evaporation by precipitation as calcium sulfate and separation by filtration.

Compound (1) has fiber reactivity and very useful dye properties. These compounds can therefore be used for dyeing or printing hydroxy-containing and / or carboxamide-containing materials. For this, the as-synthesized solution of compound (1) is used immediately in the form of a liquid composition for dyeing, with or without the addition of buffer substances beforehand and with or without preconcentration. You can also

The invention further provides the use of the compounds (1) for dyeing or printing hydroxy- and / or carboxamide-containing materials or of applying these compounds to such materials. Preferably such materials are used in the form of fibrous materials, in particular textile fibers, such as yarns, for example skeins or packages and fabrics.
This can be done according to known methods.

Hydroxy-containing materials are natural or synthetic hydroxy-containing materials, such as cellulosic fiber materials or their regenerated products and polyvinyl alcohol. The cellulosic fiber material is preferably cotton, but also other vegetable fibers, such as linen, hemp, jute and ramie fibres, and the regenerated cellulose fibers are, for example, staple viscose and filament viscose rayon. .

Carboxamide-containing materials are, for example, synthetic and natural polyamides and polyurethanes—in particular in the form of fibers—for example wool and other animal hairs, silk, leather, nylon-6,6, nylon-6, Nylon-11
And nylon-4.

The compound (1) is applied to the above materials, in particular the above fiber materials, by the techniques known for water-soluble fiber-reactive dyes on such materials according to the use provided by the invention and the water-soluble fibers. It can be fixed by known techniques for reactive dyes, for example compound (1)
Can be applied to the material in dissolved form or introduced into the material and fixed on or in the material by the action of heat or by the action of alkaline agents or by both means. Many such dyeing and fixing methods are described in the literature (for example EP-A-0181585). The compound (1) is excellent in high exhaustion and degree of fixation. Especially in the exhaust method, the compound (1) gives dyeings having a high dyeing power with a high degree of fixing even at 40 to 80 ° C.

The dyeings according to the invention, especially on cellulosic fibres, have a good fastness to the sun, not only in the dry state of the dyeings, but also in the wet state, for example when moistened with a sweat solution, and also good wet fastness, for example 60. Good washfastness at temperatures up to 95 ° C-even in the presence of perborate-
─, acid and alkaline fill, cloth dyeing and sweat fastness, good acid and alkaline sweat fastness, high water vapor resistance, good fastness to acid, water and seawater, good pleating fastness, It has ironing fastness and rubbing fastness. These compounds likewise have good resistance to acid fading when dyed materials are stored which still contain acetic acid.

[0044]

EXAMPLES The following examples serve to illustrate the invention. Parts and percentages relate to weight, unless stated otherwise. Parts by weight have the same relationship to parts by volume as kilograms to liters.

The compounds described by the formulas in the examples are described in the form of the free acids, generally they are prepared and isolated in the form of their alkali metal salts, for example lithium, sodium or potassium salts. And used in the form of their salts for dyeing.

Similarly, the starting compounds and components mentioned in the free acid form in the following examples, in particular in the table examples, can be used in the synthesis as such or in the form of their salts, preferably the alkali metal salts.

The absorption maxima (λmax) in the visible range described for the compounds of the invention were determined with their alkali metal salts in aqueous solution. In the table example, λm
The ax value is shown in parentheses by the tone column and the wavelength unit shown is nm. Example 1 1-Amino-3,6-disulfo-8-naphthol 31.
9 parts of cyanuric fluoride 1 at a pH of 7.5 and a temperature of 0 ° C. to 10 ° C. in 200 parts of water and 100 parts of ice.
Condensate with 6 parts. Then morpholine in 200 parts of water 8.
7 parts of solution are added and the second condensation reaction is brought to a pH of 8.5.
Will be carried out in. To a solution of the coupling component, a solution of a diazonium salt of 27 parts of 1-sulfo-6-carboxy-2-aminonaphthalene in about 450 parts of water, which was diazotized with sodium nitrite in a hydrochloric acid medium by a conventional method, was obtained. Add, set a pH of 5 to 6 and carry out the coupling reaction within its pH range at a temperature of about 20 ° C.

Formula (written in free acid form)

[0049]

[Chemical 25]

The new azo compound of formula (I) is salted out with sodium chloride and isolated in the sodium salt form. The compound has very good fiber-reactive dye properties. The dyeing techniques customary for fiber-reactive dyestuffs give strong dyeings and prints in fast-bluish-red shades. Examples 2 to 25 General formula (A)

[0051]

[Chemical formula 26]

Another novel azo compound corresponding to the formula (M has the above-mentioned meaning) is described in the following table examples using the general formula (A) and the symbols shown in the table. . These compounds can be prepared according to the invention, for example according to Example 1, and likewise have very good fiber-reactive dye properties. The dyeing and fixing techniques customary in the art for fiber-reactive dyestuffs give the deep, fast shades shown in the respective tables, especially on cellulosic fiber materials.

[0053]

[Table 1]

[0054]

[Table 2]

[0055]

[Table 3]

[0056]

[Table 4]

Claims (16)

[Claims] 1. A compound represented by the general formula (1): (In the formula, M is hydrogen or a salt-forming metal, K is a water-soluble coupling component (compound) H-K-N (R
⁰ ) -H is a divalent residue which does not include the group -N (R ⁰ )-, R ⁰ is hydrogen or alkyl having 1 to 4 carbon atoms, or sulfo, carboxy, sulfato, phosphato , Alkyl having 1 to 4 carbon atoms substituted by hydroxy, methoxy, ethoxy, phenyl, monosulfophenyl or disulfophenyl, G is halogen and R ¹ is hydrogen or 1 to 4 Alkyl having 1 to 4 carbon atoms or substituted by sulfo, carboxy, phosphato, sulfato, hydroxy, cyano, phenyl or sulfophenyl, or phenyl , Or sulfo, carboxy, alkyl having 1 to 4 carbon atoms, 1 not 4 alkoxy having carbon atoms, phenyl which is substituted by chlorine and / or nitro, or R ² is alkyl having a hydrogen or a 1 to 4 carbon atoms, or sulfo, carboxy, phosphato, sulfato , Alkyl having 1 to 4 carbon atoms substituted by hydroxy, cyano, phenyl or sulfophenyl, or phenyl, or 1, 2 or 3 substituents--this substituent Is 2 alkyl groups having 1 to 4 carbon atoms, 2 alkoxy groups having 1 to 4 carbon atoms, 1 bromine atom, 2 chlorine atoms, 3 sulfo groups, 2 Having 1 to 4 carbon atoms, substituted or unsubstituted by carboxy groups, 1 nitro group, hydroxy. A carboxy-substituted alkanoylamide having one alkylsulfonyl group and hydroxy, sulfato, sulfo, phosphato, by an alkanoyloxy having 2 to 5 carbon atoms or having 1 to 4 carbon atoms in the alkylene residue. Is a phenyl substituted by an alkyl residue which is substituted or unsubstituted by 1 selected from the group consisting of one alkylamino group having 1 to 4 carbon atoms; Alternatively R ² is monosulfonaphthyl, disulfonaphthyl or trisulfonaphthyl, or R ¹ and R ² are an alkylene group having 3 to 8 carbon atoms with a nitrogen atom or another hetero group and 1 to 4 Heterocyclic residue formed from two alkylene groups having 5 carbon atoms Forming a group). 2. -K- N (R ⁰ )-is represented by the general formula (2
a), (2b) or (2c) Where M and R ⁰ each have the meaning of claim 1, m is 1 or 2 and v is a direct covalent bond or a formula
- NH- CO- phenylene, - NH- CO- NH- _{phenylene, - N (CH 3) -} CO- phenylene, - N (C
H ₃₎ - CO- NH- phenylene or - NH- phenylene is a residue represented by) an azo compound of claim 1, wherein the a residue represented by. 3. -K-N (R ⁰ )-is represented by the general formula (3a) or (3b): [Wherein M has the meaning defined in claim 1 and Z ⁰ represents the general formula (3A) (Wherein G, R ¹ and R ² each have the meaning defined in claim 1) and p is zero or 1 (when zero, this group is hydrogen). The azo compound according to claim 1, which is a residue represented by: 4. A compound represented by the general formula (1A): [Wherein M and G each have the meaning defined in claim 1, p is zero or 1 (when zero, this group is hydrogen), R ³ is hydrogen, sulfo, carboxy, 1 to Alkyl having 4 carbon atoms, alkoxy having 1 to 4 carbon atoms or hydroxy, and R ⁴ is hydrogen, sulfo, carboxy, alkyl having 1 to 4 carbon atoms or 1 to 4 carbon atoms. The azo compound according to claim 1, which is an alkoxy having a carbon atom. 5. A compound represented by the general formula (1B): [Wherein M and G each have the meaning defined in claim 1, p is zero or 1 (when zero, this group is hydrogen), a is 1, 2 or 3, b Is 1, 2 or 3 and X is oxygen or --NH
And is an azo compound according to claim 1. 6. A compound represented by the general formula (1C): [Wherein M and G each have the meaning defined in claim 1, R ³ is hydrogen, sulfo, carboxy, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, or Is hydroxy and R ⁴ is hydrogen, sulfo, carboxy, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms]. 7. A compound represented by the general formula (1D): [Wherein M and G each have the meaning defined in claim 1, R ³ is hydrogen, sulfo, carboxy, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, or Hydroxy and R ⁴
Is hydrogen, sulfo, carboxy, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms], and the azo compound according to claim 1. 8. The azo compound according to claim 5, wherein a is 2, b is 2 and X is oxygen. 9. The azo compound according to claim 1, wherein R ⁰ is hydrogen. 10. The azo compound according to claim 1, wherein G is chlorine. 11. The azo compound according to claim 1, wherein G is fluorine. 12. The azo compound according to any one of claims 1 to 3 and 9 to 11, wherein --NR ¹ R ² is morpholino. 13. A general formula: The azo compound according to claim 1, which is represented by the formula: wherein M has the meaning described in claim 1. 14. A method for producing an azo compound represented by the general formula (1) according to claim 1, wherein the compound represented by the general formula (4): A diazonium compound of an amine represented by the formula (wherein M has the meaning defined in claim 1) is represented by the general formula (5): (Wherein K, R ⁰ , G, R ¹ and R ² each have the meaning defined in claim 1) or by coupling with a compound represented by the general formula (6) (Wherein each of M, K and R ⁰ has the meaning defined in claim 1) and a compound represented by the general formula (7): (Wherein G, R ¹ and R ² each have the meaning defined in claim 1) or by reacting with a compound represented by the general formula (8) (Wherein each of M, K, R ⁰ and G has the meaning defined in claim 1) and a compound represented by the general formula HNR ¹ R
^2. A method comprising reacting with an amino compound represented by the formula ² , wherein R ¹ and R ² each have the meaning defined in claim 1. 15. Use of a dye according to claim 1 or a dye prepared by the process according to claim 14 for dyeing or printing hydroxy- and / or carboxamide-containing materials, in particular textile materials. 16. A dye is applied to a hydroxy- and / or carboxamide-containing material, in particular a fibrous material, and the dye is fixed on the fibrous material by means of heat and / or by an alkaline agent, or both means. A method for dyeing or printing the above material using the dye according to claim 1 or the dye produced by the method according to claim 14.